Phenylacetyl chloride → 3-Oxo-4-phenylbutanenitrile
반응식
[C:1]([CH2:3][C:4]([OH:6])=O)#[N:2].[Li]CCCC.[C:12]1([CH2:18]C(Cl)=O)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>C1COCC1>[O:6]=[C:4]([CH2:18][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH2:3][C:1]#[N:2]참가 물질
5
실험 절차
To a solution of cyanoacetic acid (2 g, 23.5 mmol) in THF (100 mL) at −78° C. was added nBuLi (10 mL, 25.9 mmol, 2.5M in hexanes). After 30 min, phenylacetyl chloride (1.6 mL, 11.8 mmol) was added dropwise. Following an additional 30 min, the solution was partitioned between 1N HCl-Et2O and the aqueous phase was washed several times with Et2O. The combined organic fractions were dried over Na2SO4, concentrated and purified via column chromatography (silica, 30% EtOAc in hexanes) yielding the title compound (770 mg, 40%) as a tan oil: LCMS (ES) m/z 160 (M+H)+.
후처리
- waitFollowing an additional 30 min
- customthe solution was partitioned between 1N HCl-Et2O
- washthe aqueous phase was washed several times with Et2O
- dry with materialThe combined organic fractions were dried over Na2SO4
- concentrationconcentrated
- custompurified via column chromatography (silica, 30% EtOAc in hexanes)
출처 및 근거
- ORD 기록
- ord-cadee10fd3b34124a87c47e04302ddbc
- 출처 데이터셋
- uspto-grants-2013_04
- 특허 번호
- US08410158B2
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